JP2004538317A - Ｌ−リバビリンの調製方法 - Google Patents

Ｌ−リバビリンの調製方法 Download PDF

Info

Publication number: JP2004538317A
Authority: JP; Japan
Prior art keywords: group; ribavirin; mol; solvent; process according
Prior art date: 2001-07-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2003517074A

Other languages

English (en)

Japanese (ja)

Inventor

フリジエリオ，マルコ

バンフイ，アルド

ダローロ，ブルーノ

マンチーニ，アルフレド

Original Assignee

クラリアント・ライフ・サイエンス・モレキユールズ（イタリア）・エツセ・ピー・アー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-07-30

Filing date

2002-07-25

Publication date

2004-12-24

2002-07-25 Application filed by クラリアント・ライフ・サイエンス・モレキユールズ（イタリア）・エツセ・ピー・アー filed Critical クラリアント・ライフ・サイエンス・モレキユールズ（イタリア）・エツセ・ピー・アー

2004-12-24 Publication of JP2004538317A publication Critical patent/JP2004538317A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 33
IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 title claims abstract description 25
150000007517 lewis acids Chemical class 0.000 claims abstract description 18
239000002841 Lewis acid Substances 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims abstract description 10
-1 3-substituted triazole Chemical class 0.000 claims abstract description 8
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims abstract description 6
HMFHBZSHGGEWLO-OWMBCFKOSA-N L-ribofuranose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H]1O HMFHBZSHGGEWLO-OWMBCFKOSA-N 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
238000006243 chemical reaction Methods 0.000 claims description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims 1
150000003852 triazoles Chemical class 0.000 abstract description 10
238000006206 glycosylation reaction Methods 0.000 abstract description 6
230000013595 glycosylation Effects 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
229960000329 ribavirin Drugs 0.000 description 21
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 21
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 19
239000000047 product Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 9
239000012044 organic layer Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000013067 intermediate product Substances 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
230000004927 fusion Effects 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
0 CC1[C@](*)C*C(C*)C1* Chemical compound CC1[C@](*)C*C(C*)C1* 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
PYMYPHUHKUWMLA-MROZADKFSA-N aldehydo-L-ribose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-MROZADKFSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002519 immonomodulatory effect Effects 0.000 description 2
LLSQCRXJNSSQPO-UHFFFAOYSA-N methyl triazole-1-carboxylate Chemical compound COC(=O)N1C=CN=N1 LLSQCRXJNSSQPO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
UYURMLWWLDQDCD-UHFFFAOYSA-N 1h-pyrrol-2-ylsilicon Chemical compound [Si]C1=CC=CN1 UYURMLWWLDQDCD-UHFFFAOYSA-N 0.000 description 1
VTOXMULTYGBBCR-UHFFFAOYSA-N 2H-triazol-4-ylsilane Chemical class [SiH3]C1=CNN=N1 VTOXMULTYGBBCR-UHFFFAOYSA-N 0.000 description 1
208000006154 Chronic hepatitis C Diseases 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
208000005176 Hepatitis C Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
IHNHAHWGVLXCCI-FDYHWXHSSA-N [(2r,3r,4r,5s)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O IHNHAHWGVLXCCI-FDYHWXHSSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
MHSVUSZEHNVFKW-UHFFFAOYSA-N bis-4-nitrophenyl phosphate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OP(=O)(O)OC1=CC=C([N+]([O-])=O)C=C1 MHSVUSZEHNVFKW-UHFFFAOYSA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000010710 hepatitis C virus infection Diseases 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
BABPEPRNSRIYFA-UHFFFAOYSA-N silyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)O[SiH3] BABPEPRNSRIYFA-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
SJZNRVUBNAJWQA-UHFFFAOYSA-N trimethyl(2h-triazol-4-yl)silane Chemical compound C[Si](C)(C)C1=CNN=N1 SJZNRVUBNAJWQA-UHFFFAOYSA-N 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/056—Triazole or tetrazole radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

JP2003517074A 2001-07-30 2002-07-25 Ｌ−リバビリンの調製方法 Pending JP2004538317A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01830510A EP1281715B1 (fr)	2001-07-30	2001-07-30	Procédé de préparation de la ribavirine
PCT/EP2002/008330 WO2003011883A2 (fr)	2001-07-30	2002-07-25	Procede de preparation de l-ribavirine

Publications (1)

Publication Number	Publication Date
JP2004538317A true JP2004538317A (ja)	2004-12-24

Family

ID=8184638

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP2003517074A Pending JP2004538317A (ja)	2001-07-30	2002-07-25	Ｌ−リバビリンの調製方法
JP2003517075A Pending JP2004538318A (ja)	2001-07-30	2002-07-29	リバビリンの調製法

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP2003517075A Pending JP2004538318A (ja)	2001-07-30	2002-07-29	リバビリンの調製法

Country Status (13)

Country	Link
US (2)	US7285660B2 (fr)
EP (2)	EP1281715B1 (fr)
JP (2)	JP2004538317A (fr)
KR (2)	KR20040031784A (fr)
CN (2)	CN1255420C (fr)
AT (2)	ATE252594T1 (fr)
AU (1)	AU2002328974A1 (fr)
BR (2)	BR0210278A (fr)
DE (2)	DE60101056T2 (fr)
ES (2)	ES2208540T3 (fr)
HU (2)	HUP0401615A2 (fr)
MX (2)	MXPA04000382A (fr)
WO (2)	WO2003011883A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008222630A (ja) *	2007-03-12	2008-09-25	Permachem Asia Ltd	１−β−Ｄ−リボフラノシルー１，２，４−トリアゾール−３−カルボキサミドのＲ−ＩＩ型結晶の製造法

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Publication number	Priority date	Publication date	Assignee	Title
JP2005539032A (ja) *	2002-08-12	2005-12-22	エフ．ホフマン−ラ　ロシュ　アーゲー	リボフラノースの製造方法
WO2007007183A2 (fr) *	2005-07-08	2007-01-18	Aurobindo Pharma Limited	Compositions de compose antiviral
CN101891786B (zh) *	2010-08-04	2012-09-05	王明	一种利巴韦林化合物及其制法
EP2646453A1 (fr)	2010-11-30	2013-10-09	Gilead Pharmasset LLC	Composés
CN102127134B (zh) *	2010-12-02	2012-11-14	海南美兰史克制药有限公司	一种利巴韦林化合物及其方法
CN102532226B (zh) *	2010-12-15	2014-05-07	上海迪赛诺医药发展有限公司	利巴韦林晶型及其制备方法
CN109134565A (zh) *	2017-08-15	2019-01-04	李双喜	一种1/10水利巴韦林化合物及其药物组合物
CN109134566A (zh) *	2017-08-18	2019-01-04	樊艳芳	一种1/20水利巴韦林化合物
CN108484691A (zh) *	2018-06-28	2018-09-04	牡丹江师范学院	一种利巴韦林缩合物的化学合成方法
CN111647033A (zh) *	2020-06-08	2020-09-11	济南明鑫制药股份有限公司	一锅法制备利巴韦林的方法

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Publication number	Priority date	Publication date	Assignee	Title
US3798209A (en) *	1971-06-01	1974-03-19	Icn Pharmaceuticals	1,2,4-triazole nucleosides
JPS55160793A (en) *	1979-05-29	1980-12-13	Microbial Chem Res Found	Preparation of virazole
JPS5931797A (ja) *	1982-08-18	1984-02-20	Sumitomo Chem Co Ltd	新規１−置換イミダゾ−ルヌクレオシドおよびその製造法
JPS60252493A (ja) *	1984-05-25	1985-12-13	Takeda Chem Ind Ltd	シチジン誘導体の製造法
KR880011146A (ko) *	1987-03-25	1988-10-26	엠.피.젝슨	3'-아지도-3'-디옥시티미딘의 신규 제조방법 및 이러한 공정에 유용한 중간체
CN1049435C (zh) *	1994-11-09	2000-02-16	中国科学院上海药物研究所	含苯基和杂环基的青蒿素衍生物及其制备方法
EP1254911A1 (fr) *	1996-10-16	2002-11-06	ICN Pharmaceuticals, Inc.	L- nucleosides monocycliques, analogues et leurs utilisations
SK284054B6 (sk) *	1996-10-16	2004-08-03	Icn Pharmaceuticals, Inc.	Substituované triazolové nukleozidy, farmaceutický prostriedok s ich obsahom a ich použitie

2001
- 2001-07-30 EP EP01830510A patent/EP1281715B1/fr not_active Expired - Lifetime
- 2001-07-30 ES ES01830510T patent/ES2208540T3/es not_active Expired - Lifetime
- 2001-07-30 DE DE60101056T patent/DE60101056T2/de not_active Expired - Lifetime
- 2001-07-30 AT AT01830510T patent/ATE252594T1/de not_active IP Right Cessation
2002
- 2002-07-25 AT AT02764788T patent/ATE286062T1/de not_active IP Right Cessation
- 2002-07-25 EP EP02764788A patent/EP1414836B1/fr not_active Expired - Lifetime
- 2002-07-25 DE DE60202483T patent/DE60202483T2/de not_active Expired - Fee Related
- 2002-07-25 WO PCT/EP2002/008330 patent/WO2003011883A2/fr active IP Right Grant
- 2002-07-25 HU HU0401615A patent/HUP0401615A2/hu unknown
- 2002-07-25 MX MXPA04000382A patent/MXPA04000382A/es active IP Right Grant
- 2002-07-25 ES ES02764788T patent/ES2233857T3/es not_active Expired - Lifetime
- 2002-07-25 JP JP2003517074A patent/JP2004538317A/ja active Pending
- 2002-07-25 US US10/485,436 patent/US7285660B2/en not_active Expired - Fee Related
- 2002-07-25 KR KR10-2004-7001404A patent/KR20040031784A/ko not_active Application Discontinuation
- 2002-07-25 CN CNB028149246A patent/CN1255420C/zh not_active Expired - Fee Related
- 2002-07-25 AU AU2002328974A patent/AU2002328974A1/en not_active Abandoned
- 2002-07-25 BR BR0210278-1A patent/BR0210278A/pt not_active IP Right Cessation
- 2002-07-29 US US10/485,335 patent/US7285659B2/en not_active Expired - Lifetime
- 2002-07-29 CN CNB028149254A patent/CN1255421C/zh not_active Expired - Fee Related
- 2002-07-29 KR KR1020047001334A patent/KR100953031B1/ko not_active IP Right Cessation
- 2002-07-29 WO PCT/IB2002/002950 patent/WO2003011884A1/fr active Application Filing
- 2002-07-29 BR BR0209815-6A patent/BR0209815A/pt not_active IP Right Cessation
- 2002-07-29 HU HU0401899A patent/HUP0401899A2/hu unknown
- 2002-07-29 JP JP2003517075A patent/JP2004538318A/ja active Pending
- 2002-07-29 MX MXPA03010251A patent/MXPA03010251A/es active IP Right Grant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008222630A (ja) *	2007-03-12	2008-09-25	Permachem Asia Ltd	１−β−Ｄ−リボフラノシルー１，２，４−トリアゾール−３−カルボキサミドのＲ−ＩＩ型結晶の製造法

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Publication number	Publication date
KR20040021670A (ko)	2004-03-10
DE60101056D1 (de)	2003-11-27
WO2003011883A2 (fr)	2003-02-13
ES2208540T3 (es)	2004-06-16
AU2002328974A1 (en)	2003-02-17
EP1414836B1 (fr)	2004-12-29
CN1255421C (zh)	2006-05-10
WO2003011883A3 (fr)	2003-04-17
DE60101056T2 (de)	2004-05-19
CN1535277A (zh)	2004-10-06
DE60202483D1 (de)	2005-02-03
CN1535278A (zh)	2004-10-06
BR0209815A (pt)	2004-06-01
US7285660B2 (en)	2007-10-23
HUP0401899A2 (hu)	2004-12-28
KR100953031B1 (ko)	2010-04-14
HUP0401615A2 (hu)	2004-11-29
EP1414836A2 (fr)	2004-05-06
US20040192904A1 (en)	2004-09-30
EP1281715A1 (fr)	2003-02-05
ES2233857T3 (es)	2005-06-16
JP2004538318A (ja)	2004-12-24
DE60202483T2 (de)	2005-12-29
EP1281715B1 (fr)	2003-10-22
US20040176587A1 (en)	2004-09-09
ATE252594T1 (de)	2003-11-15
MXPA04000382A (es)	2004-07-23
ATE286062T1 (de)	2005-01-15
MXPA03010251A (es)	2004-03-16
WO2003011884A1 (fr)	2003-02-13
BR0210278A (pt)	2004-07-20
CN1255420C (zh)	2006-05-10
KR20040031784A (ko)	2004-04-13
US7285659B2 (en)	2007-10-23

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Publication	Publication Date	Title
JP3530218B2 (ja)	2004-05-24	▲ｎ４▼−アシル−５’−デオキシ−５−フルオロシチジン誘導体の新規製造法
JPH0313239B2 (fr)	1991-02-22
US5936077A (en)	1999-08-10	Solid phase synthesis of oligonucleotides
JP2004538317A (ja)	2004-12-24	Ｌ−リバビリンの調製方法
US4689404A (en)	1987-08-25	Production of cytosine nucleosides
CA2442979C (fr)	2010-02-16	Procede de preparation de 2'-halo beta l-arabinofuranosyl nucleosides
JP3042073B2 (ja)	2000-05-15	ヌクレオシド誘導体とその製造方法
AU2002303187A1 (en)	2003-04-03	Process for the preparation of 2'-HALO-Beta-L-arabinofuranosyl nucleosides
EP0638586A2 (fr)	1995-02-15	Dérivés de nucléosides et leur préparation
JP4691101B2 (ja)	2011-06-01	１−α−ハロ−２，２−ジフルオロ−２−デオキシ−Ｄ−リボフラノース誘導体及びその製造方法
US20090131651A1 (en)	2009-05-21	Synthesis of 2-substituted adenosines
WO1997043295A1 (fr)	1997-11-20	Derives de d-pentofuranose et leur procede de preparation
JPH07116211B2 (ja)	1995-12-13	ウラシル誘導体
JPH06135988A (ja)	1994-05-17	ヌクレオシド誘導体
JP2002121197A (ja)	2002-04-23	６−ｏ−置換ケトライド誘導体の製造方法及びその中間体
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JPH06263791A (ja)	1994-09-20	α−リバゾールの製造方法
JPH0873488A (ja)	1996-03-19	１−（２−デオキシリボフラノシル）ピリダジノン誘導体の製造法
JPH08119989A (ja)	1996-05-14	６−置換アミノプリン誘導体の新規な製法およびその中間体
KR20030078945A (ko)	2003-10-08	보호된 디옥시아데노신 및 디옥시구아노신
JPH09110893A (ja)	1997-04-28	３’−アミノ−３’−デオキシヌクレオシドの製造方法

JP2004538317A - Ｌ−リバビリンの調製方法 - Google Patents

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